3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)aniline | 946398-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)aniline
• 英文别名: 3-[(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl]sulfonylaniline
• CAS: 946398-90-9
• 化学式: C₁₈H₁₉F₄N₃O₂S
• 分子量: 417.427
• InChiKey: FPTSAUHWLVRPAJ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N,N'-bis(dimethylaminomethylene)hydrazine 、 3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)aniline 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以53%的产率得到(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methyl-1-{[3-(4H-1,2,4-triazol-4-yl)phenyl]sulfonyl}piperazine
  参考文献：
  名称：

  Piperazine Sulfonamides as Potent, Selective, and Orally Available 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors with Efficacy in the Rat Cortisone-Induced Hyperinsulinemia Model

  摘要：

  11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) is the enzyme that converts cortisone to cortisol. Evidence suggests that selective inhibition of 11 beta-HSD1 could treat diabetes and metabolic syndrome. Presented herein are the synthesis, structure-activity relationship, and in vivo evaluation of piperazine sulfonamides as 11 beta HSD1 inhibitors. Through modification of our initial lead 5a, we have identified potent and selective 11 beta-HSD1 inhibitors such as 13q and 13u with good pharmacokinetic properties.

  DOI：

  10.1021/jm8004948
• 作为产物：
  描述：

  4-(4-Fluoro-2-trifluoromethyl-phenyl)-2-methyl-1-(3-nitro-benzenesulfonyl)-piperazine 在 钯 氢气 、 乙酸乙酯 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、13.51 MPa 条件下， 反应 2.0h， 以affording 180 mg of the desired sulfonamide in >95% purity (62% yield)的产率得到3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)aniline
  参考文献：
  名称：

  11-Beta HSD1 Inhibitors

  摘要：

  本发明涉及抑制11βHSD1。

  公开号：

  US20100029648A1

文献信息

• 11-Beta HSD 1 inhibitors
  申请人：Xiang Shaoyun Jason

  公开号：US20070219198A1

  公开（公告）日：2007-09-20

  This invention relates to inhibiting 11βHSD1.

  该发明涉及抑制11βHSD1。
• 11-beta HSD1 inhibitors
  申请人：Wyeth

  公开号：US07632838B2

  公开（公告）日：2009-12-15

  This invention relates to inhibiting 11βHSD1.

  本发明涉及抑制11βHSD1的方法。
• US7632838B2
  申请人：——

  公开号：US7632838B2

  公开（公告）日：2009-12-15
• [EN] METHOD FOR PREPARING HALOGENATED AMINES<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AMINES HALOGÉNÉES
  申请人：WYETH CORP

  公开号：WO2008098103A1

  公开（公告）日：2008-08-14

  [EN] This invention relates to methods for preparing halogenated amines.
  [FR] L'invention concerne des procédés de préparation d'amines halogénées.
• Piperazine Sulfonamides as Potent, Selective, and Orally Available 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors with Efficacy in the Rat Cortisone-Induced Hyperinsulinemia Model
  作者：Jason Xiang、Zhao-Kui Wan、Huan-Qiu Li、Manus Ipek、Eva Binnun、Jill Nunez、Lihren Chen、John C. McKew、Tarek S. Mansour、Xin Xu、Vipin Suri、May Tam、Yuzhe Xing、Xiangping Li、Seung Hahm、James Tobin、Eddine Saiah

  DOI：10.1021/jm8004948

  日期：2008.7.1

  11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) is the enzyme that converts cortisone to cortisol. Evidence suggests that selective inhibition of 11 beta-HSD1 could treat diabetes and metabolic syndrome. Presented herein are the synthesis, structure-activity relationship, and in vivo evaluation of piperazine sulfonamides as 11 beta HSD1 inhibitors. Through modification of our initial lead 5a, we have identified potent and selective 11 beta-HSD1 inhibitors such as 13q and 13u with good pharmacokinetic properties.